There is no road in America quite like Route 66. Not because it is the fastest or the most scenic or the most practical, but because it is the most American. It runs 2,400 miles from the shores of Lake Michigan in Chicago all the way to the Pacific Ocean at Santa Monica, passing through eight states, dozens of small towns, and more than a century of American history along the way. People have been driving it since 1926 and the ones who do it right never quite get over it. These are the fifteen stops that make a Route 66 road trip worth every mile.
The Starting Point
Stop 1. Chicago, Illinois
Route 66 begins at the corner of Michigan Avenue and Adams Street in downtown Chicago, and the city deserves at least a full day before you point the car southwest. Walk the Magnificent Mile, eat a deep dish pizza, and stand on the shore of Lake Michigan in the morning before you leave. Chicago sets the tone for everything that follows. It is big and confident and entirely itself, and those qualities will feel familiar again when you reach the other end of the road in California.
Where it all begins — Chicago’s skyline marks Mile Zero of the most iconic road in America
Stop 2. Springfield, Illinois
Springfield is where Abraham Lincoln lived before he became president and the city wears that history with genuine pride. The Abraham Lincoln Presidential Library and Museum is one of the best presidential museums in the country, and the Lincoln Home National Historic Site gives you a sense of the man before the mythology. Springfield also has some of the best preserved Route 66 diners and drive-ins in Illinois, including the Cozy Dog Drive In, which claims to have invented the corn dog.
The Heartland
Stop 3. St. Louis, Missouri
The Gateway Arch in St. Louis is one of the most recognizable structures in America and it looks even more impressive in person than in photographs. Ride the tram to the top for a view that stretches across the Mississippi River and deep into Illinois on one side and Missouri on the other. The Old Chain of Rocks Bridge nearby is one of the most photographed sections of historic Route 66 and well worth a detour on foot.
Stop 4. Cuba, Missouri
Cuba calls itself the Route 66 Mural City and the name is well earned. The town has commissioned a series of large scale murals that tell the story of Route 66 and the surrounding region in vivid detail. It is a small town stop but one of the most visually satisfying on the entire route. The Wagon Wheel Motel here is one of the oldest continuously operating motels on Route 66 and worth a night if you can time it right.
Neon motel signs like this one lit up Route 66 from the 1940s through the 1960s — icons of the golden age of American road travel
Stop 5. Tulsa, Oklahoma
Tulsa is a larger city stop with a genuine art deco downtown that reflects the oil boom prosperity of the early twentieth century. The Cyrus Avery Centennial Plaza, known as the Route 66 Plaza, has a bronze sculpture commemorating the highway and makes for a good photograph. The Blue Dome District nearby has some of the best restaurants and bars in the city and the Woody Guthrie Center is a genuinely moving tribute to one of America’s most important folk musicians.
Stop 6. Oklahoma City, Oklahoma
Oklahoma City is a city that has rebuilt itself with remarkable resilience and the Oklahoma City National Memorial, which honors the victims of the 1995 bombing, is one of the most quietly powerful memorials in the country. Give it the time and attention it deserves. The Bricktown entertainment district nearby has good food and a canal walk that makes for a pleasant evening after a long day of driving.
Texas and the Panhandle
Stop 7. Amarillo, Texas
Amarillo is home to Cadillac Ranch, the most photographed roadside attraction on all of Route 66. Ten Cadillacs buried nose first in a wheat field, spray painted by visitors for decades, standing against the enormous Texas sky. It is free, it is open all the time, and it is genuinely unlike anything else you will see on the trip. Bring a can of spray paint and add your mark. The Big Texan Steak Ranch nearby offers a 72 ounce steak for free if you can eat the whole thing in under an hour.
Cadillac Ranch wasn’t the only one with the idea. Two states north, Jim Reinders buried 38 cars in a Nebraska field to build a full-scale replica of Stonehenge.
New Mexico
Stop 8. Santa Fe, New Mexico
Santa Fe sits just off the main Route 66 corridor but it is too significant to skip. The oldest state capital in the United States, it has an architectural style entirely its own, built from adobe and shaped by centuries of Native American, Spanish, and American influence. The Plaza at the center of the city, the Cathedral Basilica of Saint Francis of Assisi, and the Canyon Road gallery district are all worth half a day each. The food in Santa Fe is some of the best in the American Southwest.
The classic American diner where truckers, tourists, and locals all shared the same counter since the 1950s
Stop 9. Albuquerque, New Mexico
Albuquerque has the longest stretch of historic Route 66 running through its center of any city on the route, and Central Avenue is lined with neon signs, vintage motels, and diners that have barely changed since the 1950s. The Nob Hill neighborhood at the eastern end of Central Avenue has good coffee, independent bookshops, and some of the best green chile food you will eat on the entire trip.
Arizona
Stop 10. Petrified Forest National Park, Arizona
The Painted Desert and Petrified Forest along the Arizona section of Route 66 are among the most otherworldly landscapes in America. The petrified wood here is over 200 million years old and the colors of the Painted Desert shift through purple, red, orange, and white depending on the time of day and the quality of the light. Allow at least half a day and drive the entire 28 mile park road if you can.
The Petrified Forest stretch of Route 66 crosses one of the oldest landscapes in America. Where 225-million-year-old logs turned to stone long before anyone thought to build a road through them
Stop 11. Williams, Arizona
Williams is the last town in America to have been bypassed by Interstate 40 and it has used that distinction to become one of the most authentic Route 66 towns on the entire route. The historic downtown is well preserved, the diners are genuine, and the Grand Canyon Railway departs from here daily for the South Rim of the Grand Canyon. If you are going to add one detour to your Route 66 trip, the Grand Canyon is the one.
Stop 12. Seligman, Arizona
Seligman is where Route 66 nostalgia reaches its most concentrated form. The town inspired the fictional Radiator Springs in the Pixar film Cars and the main street looks almost exactly as it did in the 1950s. Angel Delgadillo, the town barber and one of the founding members of the Historic Route 66 Association, still operates his shop here and talking to him for twenty minutes is worth more than any museum exhibit on the subject.
The Mojave and California
Stop 13. Oatman, Arizona
Oatman is a former gold mining town in the Black Mountains of western Arizona where wild burros roam freely through the main street and have done so for decades. The town itself is a preserved piece of old west americana, with wooden storefronts, saloon fronts, and a main street that has barely changed in fifty years. The drive through the Black Mountains on the old road to get there is one of the most dramatic and least driven sections of the entire route.
Even when the door was still half open. We didn’t go in, but we wanted to
Stop 14. Barstow, California
Barstow marks the beginning of the final California stretch and the point where the Mojave Desert opens up into something vast and quietly beautiful. The Route 66 Mother Road Museum here is small but genuinely informative, and the Harvey House railroad depot it occupies is a beautiful piece of early twentieth century American architecture. From Barstow the road runs through the high desert toward San Bernardino and then down into the Los Angeles basin.
The End of the Road
Stop 15. Santa Monica, California
Route 66 ends at the Santa Monica Pier, where Will Rogers Highway meets the Pacific Ocean and the continent runs out of land. Stand at the end of the pier on a clear evening and look west across the water. The sun goes down in roughly the direction you have been driving for two thousand miles and the feeling of having crossed the country on the old road is one that stays with you for a long time.
Nothing behind me, everything ahead of me.
— Jack Kerouac
